Citric Acid → HCID 25239132, compound

HRID 601640Notes

Reaction equation

HRID 601640 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11](=[O:13])[NH:30][C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6385Tert-ButylamineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 25239132HCID 25239132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-tert-Butoxycarbonylamino-propionic acid (0.5 g, 2.64 mmol) in DCM (5 ml) under an inert atmosphere is treated with 1-hydroxy-7-azabenzatriazole (0.108 g, 0.79 mmol) followed by water soluble carbodiimide (0.491 g, 3.17 mnol) and tert-butylamine (0.305 ml, 2.91 mmol). The reaction mixture is stirred at room temperature for 3 hours and then citric acid (10 ml, 0.5 M) is added to the solution and extracted with DCM (2×10 ml). The combined organic layers are washed with brine (10 ml) and dried over MgSO4. After filtration, the solvent is removed in vacuo to yield the titled compound as an oil.

Workup

  1. extractionextracted with DCM (2×10 ml)
  2. washThe combined organic layers are washed with brine (10 ml)
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7fb029a696cf44e2a90d132d2a1366a8
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Reaction notes

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